Tetra-(5-acetylamino-7-heptyloxy)-anthraquinonoporphyrazines of copper and cobalt

FIELD: chemistry.

SUBSTANCE: invention relates to tetra-(5-acetylamino-7-heptyloxy)anthraquinonoporphyrazines of copper and cobalt of formula .

EFFECT: obtained compounds can be used as dyes and catalysts.

4 ex, 5 dwg,

 

Introduction

The invention relates to the chemical industry, namely, to obtain new derivatives metalloporphyrin - Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper and cobalt, which can be used as dyes, catalysts, and other fields of science and technology.

The level of technology

The richest possibility of chemical modification of the compounds porphyrinogen series allows you to use them for different purpose, such as lightfastness of dyes and pigments [B. I. Stepanov introduction to the chemistry and technology of organic dyes. Educational. for universities. 3rd ed. Rev. and ext. M.: Chemistry, 1984, 592 S.], as catalysts for various processes [M. R. Tarasevich, Radyushkin K.A. Catalysis and electrocatalysis by metalloporphyrins. M.: Nauka, 1982. 168 C., Stuzhinskaya TL Catalysts for the oxidation of sulfur compounds based on derivatives of phthalocyanine cobalt: Diss.... Kida. chem. Sciences. Novosibirsk. INSTITUTE OF CATALYSIS SB RAS. 1999. 131 S.].

Known Tetra-4-[(4'-octyloxybenzoic)oxy]copper phthalocyanine [Synthesis and mesomorphic properties alkoxybenzenes tetraamine(hydroxy)phthalocyanine copper / Terracina T.V., Maizlish V.E., Shaposhnikov G.P., jarnikova N., Bykova V.V., Usol'tseva N.V. // Liquid crystals and their practical use. 2005. Issue 3-4 (13-14). P.23] formula

However, the use of Tetra-4-[(4'-octyloxybenzoic)oxy]-copper phthalocyanine as the dye does not allow you to get rich color and uniformity of colors.

The closest structural analogues of cobalt and copper complexes of the claimed compounds are Tetra-(5,8-dihydroxy)intrahemispheric cobalt and copper [Borisov A.V., Maizlish V.E., Shaposhnikov G.P. Way to obtain complexes of Tetra-(5,8-dihydroxy)intrahemispheric. Pat. RF 2277098. BI No. 15 of 27.05.06.] formula

However, these compounds do not possess solubility in organic media, therefore cannot be used as dyes and exhibit low catalytic activity.

The invention

Inventive task was to search for new derivatives metalloporphyrins, which would have the properties of the dye and, in addition, could be used as catalysts. The problem is solved copper or cobalt complexes of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric formula

The structure of these compounds proved by data of elemental analysis, IR and electronic spectroscopy.

Thus, the IR spectrum of the copper complex (figure 1) it is possible to allocate a number of common absorption bands with nezamedin the m analog [.Sakamoto, E.Ohno Synthesis of Cobalt Phthalocyanine Derivatives and their Cyclic Voltammograms // Dyes and Pigments. 1997. Vol.35. # 4. P.375-386].

In the electronic absorption spectra of the Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper and cobalt intensive absorption at 744-746 nm in concentrated sulfuric acid, at 682-683 nm in dimethylformamide, at 692 nm in o-xylene, at 684-685 nm in chloroform (2, 3).

Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper and cobalt are substances dark green color. These compounds are soluble in concentrated sulfuric acid, dimethylformamide, xylene, chloroform. Copper and cobalt complexes of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric can be used as dyes and catalysts.

Information regarding the playback of the invention.

To implement the method using the following ingredients:

- calcium carbonate - GOST 10690-73,

- heptyl bromide-GOST 28296-89,

- Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt.

The claimed compounds produced by interaction of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper or cobalt with methyl-heptyl.

Because Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt are new compounds and are not manufactured industrial the spine, they were obtained in the following way: first, carry out the acylation with acetic anhydride m-anisidine, then the 1-acetylamino-3-methoxybenzoyl subjected to interaction with the dianhydride pyromellitic acid in the presence of anhydrous aluminum chloride, followed by intramolecular cyclization by treatment received in the second stage 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid concentrated sulfuric acid (monohydrate). In the intramolecular cyclization receive 2,3-dicarboxy-5-acetylamino-7-methoxyacridine, from which then the method of the paid synthesis and subsequent hydrolysis get Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt.

Stage 1. Synthesis of 1-acetylamino-3-methoxybenzene.

In a flask equipped with a stirrer, thermometer and reflux condenser, dissolve 6.1 g (0.05 mol) of m-anisidine in 10 ml of toluene. Then placed in the flask and the solution gently for 15 minutes, poured 5.1 ml (0.5 mol) of acetic anhydride with heating of the reaction mass. After adding the total amount of acetic anhydride mixture is allowed to cool. The precipitated crystals acicular forms is filtered on a Buechner funnel. Washed with toluene in small portions until no odor of acetic acid, washed with water until it is General environment and dried at a temperature of 75-80°C.

Output 1-acetylamino-3-methoxybenzoyl 6.5,

Stage 2. Synthesis of 5-[(2'-acetylamino-4'-methoxy)benzoyl]-trimelitic acid.

In a three-neck flask with a capacity of 100 ml equipped with a stirrer, reflux condenser and thermometer, is placed 10.0 g (0.046 mole) of the dianhydride pyromellitic acid, 8.42 g (0.051 mol) of 1-acetylamino-3-methoxybenzene and 20 ml of heptane. The mass is heated to 50°C. and with stirring add 16.12 g (0.119 mol) of anhydrous aluminum chloride. Stand 3 hours at boiling of the reaction mass (≈100°C), and after removal of the heptane another 6 hours at 120-130°C. After cooling, to the reaction mass is added 50 ml of water and after soaking for 30 minutes, add hot soda solution and separating the precipitated precipitate aluminum hydroxide. To the aqueous layer of the filtrate add hydrochloric acid to pH 3-4. Precipitation 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid. It is filtered off, washed with water until neutral environment and dried at a temperature of 75-80°C.

Output 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimelitic acid 7.8,

Stage 3. Synthesis of 2,3-dicarboxy-5-acetylamino-7-methoxyacridine.

In a flask with a volume of 200 ml equipped with a stirrer and thermometer, was placed 10 ml monohydrate and heated to 130°C. and Then for 15 minutes with vigorous stirring, add 5 g of the obtained 5-[(2'-acetylamino-4'-methoxy)benzoyl]trimellitate key is lots the temperature was raised to 150°C and maintained for 5 hours. The mass after cooling with stirring, poured into 200 ml of water, filtered, washed with a large amount of ice-cold water, dissolve in soda solution and acidified with hydrochloric acid. The precipitate is filtered off and washed with water until the disappearance of the chloride ions. Such processing is repeated twice. Dried at 100°C.

The yield of 2,3-dicarboxy-5-acetylamino-7-methoxyacridine 4.1, TPL=3600C.

Stage 4. Synthesis of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper and cobalt.

In a quartz ampoule put the pounded mixture of 0.23 g (0.60 mmol) of 2,3-dicarboxy-5-acetylamino-7-methoxyacridine 0.24 g (4.00 mmol) of urea, 0.036 g (0.18 mmol) of copper acetate or 0.037 g (0.18 mmol) of cobalt acetate, 0.02 g (0.40 mmol) of ammonium chloride and 0.002 g (0.01 mmol) of ammonium molybdate. The mass is slowly heated to 180°C for one hour and incubated for 3 hours. The resulting suspension is filtered, periostat of sulfuric acid and washed to conventional Soxhlet extractions with acetone for 10 hours. Dried at 100°C.

The output of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper 0.13,

The output of Tetra-(5-acetylamino-7-methoxy)intrahemispheric cobalt 0.12,

Stage 5. Synthesis of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper and cobalt.

In a flask with a capacity of 25 ml with 10 ml of 1%aqueous process is as sodium hydroxide introduce 0.1 g of Tetra-(5-acetylamino-7-methoxy)intrahemispheric copper or cobalt and heated in a water bath at 80°C for 40-50 minutes. The resulting suspension is filtered, periostat of sulfuric acid and washed to conventional Soxhlet extractions with acetone for 10 hours. Dried at 100°C. the Dark green substance, possess solubility in DMF, 1%sodium hydroxide solution, concentrated sulfuric acid.

The output of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper, 0.09,

The output of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric cobalt 0.08,

Example 1. Synthesis of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper and cobalt.

In odnogolosy flask of 50 ml equipped with a reflux condenser, a load 15 ml of DMF, 0.12 g of potash (K2CO3), 0.05 g of Tetra-(5-acetylamino-7-hydroxy)intrahemispheric copper or cobalt, 4 ml of methyl heptyl (C7H15Br). The reaction mass is boiled for 24 hours, then poured into cold water, filtered and washed with hexane until no odor of methyl heptane, then with water, with acetone and subjected to sediment column chromatography, the adsorbent is alumina II degree of activity, eluent - chloroform.

The output of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric copper, 0.04 g (85%).

The output of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric cobalt 0.04 g (84%).

Dark green substance, possess solubility in DMF, chloroform, o-xylene, concentrated the agreement acid.

ESP copper complex in chloroform, λmaxnm: 358, 641, 683 (figure 2).

ESP cobalt complex in chloroform, λmaxnm: 358, 641, 684 (Fig 3).

Found, %:With 67.52; H 5.13; N, 9.30. C100N12H92O16Cu.
With 67.56; H 5.15; N, 9.50. C100N12H92O16Co.
Calculated, %:With 67.42; N, 5.21; N, 9.44. C100N12H92O16Cu.
With 67.43; N, 5.21; N, 9.44. C100N12H92O16Co.

Example 2. The use of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper as a dye for dyeing polyethylene and polystyrene.

The dyeing of polyethylene. 2 g of polyethylene is placed in a porcelain Cup and heated to melt, then pour in a solution of 5 ml of chloroform, which is dissolved 0.003 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper. Stand when heated to a complete removal of chloroform and the resulting mass is poured into the form.

The sample is attached (see figure 5).

Dyeing polystyrene. 0.1 g of polystyrene are dissolved by heating in 1 ml of benzene and add 1 ml of benzene, which is dissolved 0.002 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper. The solution is boiled for 3 minutes and the resulting mass you have the more in shape.

The sample is attached (see figure 5).

Example 3. The use of Tetra-(5-acetylamino-7-heptyloxy)-intrahemispheric cobalt as a dye for dyeing polyethylene and polystyrene.

The dyeing of polyethylene. 2 g of polyethylene is placed in a porcelain Cup and heated to melt, then pour in a solution of 5 ml of chloroform, which is dissolved 0.003 g of Tetra-(5-atsetamino-7-heptyloxy)intrahemispheric cobalt. Stand when heated to a complete removal of chloroform and the resulting mass is poured into the form.

The sample is attached (see figure 5).

Dyeing polystyrene. 0.1 g of polystyrene are dissolved by heating in 1 ml of benzene and add 1 ml of benzene, which is dissolved 0.002 g of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric cobalt. The solution is boiled for 3 minutes and the resulting mass is poured into the form.

The sample is attached (see figure 5).

Example 4. The use of Tetra-(5-acetylamino-7-heptyloxy)-intrahemispheric cobalt as catalyst for the oxidation of mercaptans.

Study of catalytic activity of the cobalt complex of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric conducted 0.02 M solution diethyldithiocarbamate sodium (DETC) on the setup depicted in figure 4.

For the preparation of heterogeneous catalyst solution of cobalt is the first complex of Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric in DMF to a concentration of 0.01 mol/l in 50 ml immersed and fully impregnate the sample of non-woven polypropylene weight of 2, Then the polypropylene remove and immerse in water to remove the organic solvent. When this happens fast crystallization and precipitation of the cobalt complex on the surface of the polypropylene fibers. The concentration of the complex on the surface of non-woven material such treatment is 1.5·10-5mol per 1 g of polypropylene. Thus obtained heterogeneous catalyst is placed in a glass DADD equipped with a CIRCULATOR pump 650 capacity 600 l/h to supply air required for oxidation at a constant speed of 2 l/min After the reaction mixture in the glass will be set at a constant temperature, select a sample of 2 ml to determine the initial concentration DADD and breathable. The time of air supply is taken for the start of the reaction. During the reaction after a certain period of time take samples of 2 ml for spectrometric determination of current concentration DADD.

The effective rate constant for the oxidation DADD is 2.6±0.4 sec-1.

Tetra-(5-acetylamino-7-heptyloxy)intrahemispheric copper and cobalt formula:



 

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